63 Chesterfield Rd, Williamsburg, MA 01096
Siding in Chesterfield, Massachusetts
Compare contractors serving Chesterfield, Hampshire County — call them directly, or send one request and let the ones who want the job come to you.
30 contractors serving Chesterfield.
Contractors serving Chesterfield
Claimed listings within 5 miles come first, then the rest by rating, then distance. Google ratings as of October 2026. How we list and rank contractors
- Guiel ConstructionServes Chesterfield · 4.4 mi★★★★★5.0 Google rating
- GL FOUR STAR HOME IMPROVEMENT INCServes Chesterfield · 11.0 mi★★★★★5.0 Google rating
80 Damon Rd # 1, Northampton, MA 01060
- Stone Mountain Roofing LLCServes Chesterfield · 11.1 mi★★★★★5.0 Google rating
156 Northampton St, Easthampton, MA 01027
- Yeoman Design BuildServes Chesterfield · 14.5 mi★★★★★5.0 Google rating
123 Sandgully Rd N, South Deerfield, MA 01373
- Hometown Metal RoofingServes Chesterfield · 16.1 mi★★★★★5.0 Google rating
627 Southampton Rd, Westfield, MA 01085
- NextGen RoofingServes Chesterfield · 16.3 mi★★★★★5.0 Google rating
549 Southampton Rd, Westfield, MA 01085
- Mayers Enterprise LLCServes Chesterfield · 16.6 mi★★★★★5.0 Google rating
427 Beech St, Holyoke, MA 01040
- Integrity Development & ConstructionServes Chesterfield · 16.6 mi★★★★★5.0 Google rating
110 Pulpit Hill Rd, Amherst, MA 01002
- Cedar Falls ConstructionServes Chesterfield · 17.9 mi★★★★★5.0 Google rating
209 Prospect St, Chicopee, MA 01013
- 3D Home ImprovementsServes Chesterfield · 18.1 mi★★★★★5.0 Google rating
74 Old Holyoke Rd, Westfield, MA 01085
- d. hayward restorationServes Chesterfield · 18.5 mi★★★★★5.0 Google rating
111 River St, Greenfield, MA 01301
- BRJ BuildersServes Chesterfield · 19.0 mi★★★★★5.0 Google rating
30 Olive St, Greenfield, MA 01301
- Major Home Improvements LLC - RoofingServes Chesterfield · 19.1 mi★★★★★5.0 Google rating
22 Verona St, Westfield, MA 01085
- Chamberland CedarServes Chesterfield · 19.9 mi★★★★★5.0 Google rating
14 Exchange St, Chicopee, MA 01013
- A-Z Exteriors, INCServes Chesterfield · 19.9 mi★★★★★5.0 Google rating
258 Hillside Rd, Southwick, MA 01077
- JP Carroll RoofingServes Chesterfield · 16.2 mi★★★★★4.9 Google rating
20a Turnpike Industrial Rd, Westfield, MA 01085
- Green CollarServes Chesterfield · 16.9 mi★★★★★4.9 Google rating
48 Lamb St, South Hadley, MA 01075
- Nova VC ConstructionServes Chesterfield · 19.0 mi★★★★★4.9 Google rating
591 Grattan St, Chicopee, MA 01020
- Sexton Roofing & SidingServes Chesterfield · 10.6 mi★★★★★4.8 Google rating
6 Church Ave, West Hatfield, MA 01088
- Dicky Matos Roofing IncServes Chesterfield · 16.9 mi★★★★★4.8 Google rating
23 Hadley Mill Rd, Holyoke, MA 01040
- Alliance Home Improvement IncServes Chesterfield · 18.1 mi★★★★★4.8 Google rating
375 Chicopee St, Chicopee, MA 01013
- Yankee HomeServes Chesterfield · 19.5 mi★★★★★4.8 Google rating
36 Justin Dr, Chicopee, MA 01022
- Berkshire Home Pros, IncServes Chesterfield · 18.2 mi★★★★★4.7 Google rating
90 Flansburg Ave, Dalton, MA 01226
- First Generation Construction LLCServes Chesterfield · 19.0 mi★★★★★4.7 Google rating
324 Main St, Greenfield, MA 01301
- Chagnon Building & Remodeling, LLCServes Chesterfield · 14.9 mi★★★★★4.6 Google rating
91 Stockbridge St, Hadley, MA 01035
- Keith G. Roy Construction, Inc.Serves Chesterfield · 19.2 mi★★★★☆4.3 Google rating
54 Mainline Dr, Westfield, MA 01085
- N. Riley Construction, Inc.Serves Chesterfield · 18.9 mi★★★★☆4.1 Google rating
621 Grattan St, Chicopee, MA 01020
- The Axxion Company, LLCServes Chesterfield · 16.8 mi★★★★☆4.0 Google rating
67 Suffolk St, Holyoke, MA 01040
- Hawkins RoofingServes Chesterfield · 16.9 mi★★★★☆4.0 Google rating
15 Sunrise Ave, Deerfield, MA 01342
- Serves Chesterfield · 17.5 mi
115 Market Hill Rd, Amherst, MA 01002
Siding in Chesterfield — what to know
Energy & rebates
Chesterfield is served by Eversource, so homeowners are fully Mass Save eligible. The siding isn't rebated, but pulling the cladding is the cheapest window to insulate cavities, air-seal, and on the exposed upper sites and gorge-edge homes, add continuous exterior insulation.
Mass Save typically covers weatherization at 75% or more after a free Home Energy Assessment, and the 0% HEAT Loan can finance qualifying envelope work. The 1960s–80s ranches and contemporaries across Chesterfield were built to that era's loose insulation standards, and many older farmhouses have empty cavities. The rebated envelope work behind new siding is usually where the comfort and bill improvement come from.
Permits in Chesterfield
Chesterfield requires a building permit for residential re-siding through the town Building Department. The Westfield River corridor (a Wild & Scenic river), Chesterfield Gorge, and the network of tributary brooks put many parcels inside Wetlands Protection Act buffer zones, and Conservation Commission review is common; Wild & Scenic status can add review for ground-disturbing work along the river. With a 53-year median build, lead RRP applies to the older stock, and asbestos-cement shingle still turns up on mid-century homes.
Where a permit is required, siding work in Chesterfield is filed with the Chesterfield Building Department; see the Chesterfield Building Department’s contact, portal and who pulls the permit on permits.llc.
Typical project cost
Re-siding a typical Chesterfield single-family runs roughly $10,000–$21,000 for vinyl, $12,500–$25,000 for insulated vinyl, and $16,500–$36,000 for fiber-cement. Cedar on the older farmhouses generally lands $20,000–$50,000 for a full wrap. Western Hampshire hilltown labor sits below the Northampton baseline. Chesterfield-specific drivers are gorge-edge access, long back-road driveways, and the higher fastener spec for the upper exposures.
About Chesterfield homes
Chesterfield is a Hampshire County hill town of about 996 residents across roughly 504 housing units, on the ridges west of Northampton above the Westfield River gorge. The town is largely forest, with Chesterfield Gorge and the Westfield River Wild & Scenic corridor defining the dramatic terrain on its eastern edge.
The median home is around 53 years old, with a stock that mixes 19th-century farmhouses along the original roads, 1960s–80s contemporaries and ranches on subdivided land, and newer custom builds on the back roads. Elevations across town range broadly, and gorge-edge sites add a real moisture and exposure profile that ordinary hill-town conditions don't quite capture.
Common questions — Siding in Chesterfield
- Does Mass Save cover insulation behind new siding in Chesterfield?
- Yes. Chesterfield is Eversource territory, so homeowners qualify for the full Mass Save program. The siding isn't rebated, but cavity insulation and air-sealing behind it are typically subsidized at 75%+ after a free Home Energy Assessment.
- I'm on a gorge-edge lot. Does that change the siding spec?
- Often yes. Gorge-side homes get more humidity, more freeze-thaw cycling, and more wind. Premium WRB, generous flashing details, and either fiber-cement or insulated vinyl tend to age better than basic vinyl on those exposures.
- Will a project near the Westfield River need Conservation review?
- Often yes. The river is Wild & Scenic, and many adjacent parcels sit inside Wetlands Protection Act buffer zones. Exterior work involving staging or grading can trigger review.
- Is asbestos siding common on Chesterfield homes?
- On the mid-century capes and ranches, yes — asbestos-cement shingle was widely used through the 1960s. A licensed inspector should sample any suspect material before demo.
- Do I need a permit to re-side in Chesterfield?
- Yes. The Chesterfield Building Department requires a permit, and a reputable contractor handles the paperwork and inspections.
